Catalysis by polymer-bound rhodium carbonyl clusters. Selective hydrogenation of α,β-unsaturated aldehydes to allylic alcohols in the presence of H2 and CO

Organometallics

Volumn 15, Issue 15, 1996, Pages 3247-3249

  Kaneda, Kiyotomi ^a   Mizugaki, Tomoo ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000392028     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om960094e     Document Type: Article

References (30)

1. For recent books and reviews, see: (a) Gates, B. C. Chem. Rev. 1995, 95, 511. (b) Lewis, L. N. Chem. Rev. 1993, 93, 2693. (c) Süss-Fink, G.; Meister, G. In Advances in Organometallic Chemistry; Stone, E. G., West, R., Eds.; Academic Press: San Diego, CA, 1993; Vol. 35, p 41. (d) Shriver, D. F., Kaesz, H. D., Adams, R. D., Eds. The Chemistry of Metal Cluster Complexes; VCH: New York, 1990.
2. For recent books and reviews, see: (a) Gates, B. C. Chem. Rev. 1995, 95, 511. (b) Lewis, L. N. Chem. Rev. 1993, 93, 2693. (c) Süss-Fink, G.; Meister, G. In Advances in Organometallic Chemistry; Stone, E. G., West, R., Eds.; Academic Press: San Diego, CA, 1993; Vol. 35, p 41. (d) Shriver, D. F., Kaesz, H. D., Adams, R. D., Eds. The Chemistry of Metal Cluster Complexes; VCH: New York, 1990.
3. For recent books and reviews, see: (a) Gates, B. C. Chem. Rev. 1995, 95, 511. (b) Lewis, L. N. Chem. Rev. 1993, 93, 2693. (c) Süss-Fink, G.; Meister, G. In Advances in Organometallic Chemistry; Stone, E. G., West, R., Eds.; Academic Press: San Diego, CA, 1993; Vol. 35, p 41. (d) Shriver, D. F., Kaesz, H. D., Adams, R. D., Eds. The Chemistry of Metal Cluster Complexes; VCH: New York, 1990.
4. For recent books and reviews, see: (a) Gates, B. C. Chem. Rev. 1995, 95, 511. (b) Lewis, L. N. Chem. Rev. 1993, 93, 2693. (c) Süss-Fink, G.; Meister, G. In Advances in Organometallic Chemistry; Stone, E. G., West, R., Eds.; Academic Press: San Diego, CA, 1993; Vol. 35, p 41. (d) Shriver, D. F., Kaesz, H. D., Adams, R. D., Eds. The Chemistry of Metal Cluster Complexes; VCH: New York, 1990.
5. Kaneda, K.; Yasumura, M.; Imanaka, T.; Teranishi, S. J. Chem. Soc., Chem. Commun. 1982, 935.
6. Rylander, P. N. Hydrogenation Methods; Academic Press: London, 1985; p 70.
7. For typical metal complex catalysts for hydrogenation of α,β-unsaturated carbonyl compounds to allylic alcohols, see: (a) Planeix, J. M.; Coustel, N.; Coq, B.; Brotons, V.; Kumbhar, P. S.; Dutartre, R.; Geneste, P.; Bernier, P.; Ajayan, P. M. J. Am. Chem. Soc. 1994, 116, 7935. (b) Fache, E.; Mercier, C.; Pagnier, N.; Despeyroux, B.; Panster, P. J. Mol. Catal. 1993, 79, 117. (c) Lau, C. P.; Ren, C. Y.; Chu, M. T.; Yeung, C. H. J. Mol. Catal. 1991, 65, 287. (d) Grosselin, J. M.; Mercier, C.; Allmang, G.; Gruss, F. Organometallics 1991, 10, 2126. (e) Mizoloki, T.; Seki, K.; Meguro, S.; Ozaki, A. Bull. Chem. Soc. Jpn. 1977, 50, 2148.
8. For typical metal complex catalysts for hydrogenation of α,β-unsaturated carbonyl compounds to allylic alcohols, see: (a) Planeix, J. M.; Coustel, N.; Coq, B.; Brotons, V.; Kumbhar, P. S.; Dutartre, R.; Geneste, P.; Bernier, P.; Ajayan, P. M. J. Am. Chem. Soc. 1994, 116, 7935. (b) Fache, E.; Mercier, C.; Pagnier, N.; Despeyroux, B.; Panster, P. J. Mol. Catal. 1993, 79, 117. (c) Lau, C. P.; Ren, C. Y.; Chu, M. T.; Yeung, C. H. J. Mol. Catal. 1991, 65, 287. (d) Grosselin, J. M.; Mercier, C.; Allmang, G.; Gruss, F. Organometallics 1991, 10, 2126. (e) Mizoloki, T.; Seki, K.; Meguro, S.; Ozaki, A. Bull. Chem. Soc. Jpn. 1977, 50, 2148.
9. For typical metal complex catalysts for hydrogenation of α,β-unsaturated carbonyl compounds to allylic alcohols, see: (a) Planeix, J. M.; Coustel, N.; Coq, B.; Brotons, V.; Kumbhar, P. S.; Dutartre, R.; Geneste, P.; Bernier, P.; Ajayan, P. M. J. Am. Chem. Soc. 1994, 116, 7935. (b) Fache, E.; Mercier, C.; Pagnier, N.; Despeyroux, B.; Panster, P. J. Mol. Catal. 1993, 79, 117. (c) Lau, C. P.; Ren, C. Y.; Chu, M. T.; Yeung, C. H. J. Mol. Catal. 1991, 65, 287. (d) Grosselin, J. M.; Mercier, C.; Allmang, G.; Gruss, F. Organometallics 1991, 10, 2126. (e) Mizoloki, T.; Seki, K.; Meguro, S.; Ozaki, A. Bull. Chem. Soc. Jpn. 1977, 50, 2148.
10. For typical metal complex catalysts for hydrogenation of α,β-unsaturated carbonyl compounds to allylic alcohols, see: (a) Planeix, J. M.; Coustel, N.; Coq, B.; Brotons, V.; Kumbhar, P. S.; Dutartre, R.; Geneste, P.; Bernier, P.; Ajayan, P. M. J. Am. Chem. Soc. 1994, 116, 7935. (b) Fache, E.; Mercier, C.; Pagnier, N.; Despeyroux, B.; Panster, P. J. Mol. Catal. 1993, 79, 117. (c) Lau, C. P.; Ren, C. Y.; Chu, M. T.; Yeung, C. H. J. Mol. Catal. 1991, 65, 287. (d) Grosselin, J. M.; Mercier, C.; Allmang, G.; Gruss, F. Organometallics 1991, 10, 2126. (e) Mizoloki, T.; Seki, K.; Meguro, S.; Ozaki, A. Bull. Chem. Soc. Jpn. 1977, 50, 2148.
11. For typical metal complex catalysts for hydrogenation of α,β-unsaturated carbonyl compounds to allylic alcohols, see: (a) Planeix, J. M.; Coustel, N.; Coq, B.; Brotons, V.; Kumbhar, P. S.; Dutartre, R.; Geneste, P.; Bernier, P.; Ajayan, P. M. J. Am. Chem. Soc. 1994, 116, 7935. (b) Fache, E.; Mercier, C.; Pagnier, N.; Despeyroux, B.; Panster, P. J. Mol. Catal. 1993, 79, 117. (c) Lau, C. P.; Ren, C. Y.; Chu, M. T.; Yeung, C. H. J. Mol. Catal. 1991, 65, 287. (d) Grosselin, J. M.; Mercier, C.; Allmang, G.; Gruss, F. Organometallics 1991, 10, 2126. (e) Mizoloki, T.; Seki, K.; Meguro, S.; Ozaki, A. Bull. Chem. Soc. Jpn. 1977, 50, 2148.
12. Lieto, J.; Milstein, R.; Albright, R. L.; Minkiewicz, J. V.; Gates, B. C. CHEMTECH 1983, 13, 46.
13. Meyers, A. I.; Nabeya, A.; Adickes, H. W.; Politzer, I. R.; Malone, G. R.; Kovelesky, A. C.; Nolen, R. L.; Portnoy, R. C. J. Org. Chem. 1973, 38, 36.
14. Ramage, R. G.; Griffiths, J.; Shutt, F. E.; Sweeney, J. N. A. J. Chem. Soc., Perkin Trans, 1 1984, 7, 1531.
15. 2-.
16. 2-.
17. 2-.
18. -1), see: (a) Fumagalli, A.; Koetzle, T. F.; Takusagawa, F.; Chini, P.; Martinengo, S.; Heaton, B. T. J. Am. Chem. Soc. 1980, 102, 1740. (b) Chini, P.; Martinengo, S. Inorg. Chim. Acta 1969, 3, 21. (c) Kawi, S.; Gates, B. C. Inorg. Chem. 1994, 33, 50310) In the case of the heterogeneous reaction, THF is not an excellent solvent: after the reduction in a THF solvent, the filtrate of the reaction mixture was reddish brown, which shows elution of Rh complexes from the aminated polymer. Detailed results of the homogeneous catalysis are given in the Supporting Information.
19. -1), see: (a) Fumagalli, A.; Koetzle, T. F.; Takusagawa, F.; Chini, P.; Martinengo, S.; Heaton, B. T. J. Am. Chem. Soc. 1980, 102, 1740. (b) Chini, P.; Martinengo, S. Inorg. Chim. Acta 1969, 3, 21. (c) Kawi, S.; Gates, B. C. Inorg. Chem. 1994, 33, 50310) In the case of the heterogeneous reaction, THF is not an excellent solvent: after the reduction in a THF solvent, the filtrate of the reaction mixture was reddish brown, which shows elution of Rh complexes from the aminated polymer. Detailed results of the homogeneous catalysis are given in the Supporting Information.
20. -1), see: (a) Fumagalli, A.; Koetzle, T. F.; Takusagawa, F.; Chini, P.; Martinengo, S.; Heaton, B. T. J. Am. Chem. Soc. 1980, 102, 1740. (b) Chini, P.; Martinengo, S. Inorg. Chim. Acta 1969, 3, 21. (c) Kawi, S.; Gates, B. C. Inorg. Chem. 1994, 33, 50310) In the case of the heterogeneous reaction, THF is not an excellent solvent: after the reduction in a THF solvent, the filtrate of the reaction mixture was reddish brown, which shows elution of Rh complexes from the aminated polymer. Detailed results of the homogeneous catalysis are given in the Supporting Information.
21. 1-Octene as a common oelfin was not reduced under the above conditions. In the case of α,β-unsaturated aldehydes, reduction of olefinic functions might not occur by 1,2-addition of metal-hydride to olefinic carbons but by 1,4-addition.
22. Isomerization of allylic alcohols to saturated aldehydes easily occurred in the presence of metal catalysts; see: Süss-Fink, G.; Meister, G. In Advances in Organometallic Chemistry; Stone, E. G., West, R., Eds.; Academic Press: San Diego, CA, 1993; Vol. 35, p 107.
23. (a) Heaton, B. T.; Strona, L.; Martinengo, S.; Strumolo, D.; Goodfellow, R. J.; Sadler, I. H. J. Chem. Soc., Dalton Trans. 1982, 1499.
24. (b) Dufour, P.; Huang, L.; Choplin, A.; Sanchez-Delgado, S. G.; Theolier, A.; Basset, J. M. J. Organomet. Chem. 1988, 354, 243.
25. (a) Heinekey, D. M.; Oldham, W. J., Jr. Chem. Rev. 1993, 93, 913.
26. (b) Jessop, P. G.; Morris, R. H. Coord. Chem. Rev. 1992, 121, 155.
27. (c) Collmann, J. P.; Hegedus, L. S. Prnciples and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1980; p 319.
28. Books and review on polymer-bound metal complex catalysts: (a) Gates, B. C. Catalytic Chemistry; Wiley: New York, 1992. (b) Sheats, J. E., Carraher, C. E., Jr., Pittman, C. E., Jr., Zeldin, M., Currell, B., Eds. Inorganic and Metal-Containing Polymeric Materials; Plenum Press: New York, 1990. (c) Bergbreiter, D. E. CHEMTECH 1987, 17, 686.
29. Books and review on polymer-bound metal complex catalysts: (a) Gates, B. C. Catalytic Chemistry; Wiley: New York, 1992. (b) Sheats, J. E., Carraher, C. E., Jr., Pittman, C. E., Jr., Zeldin, M., Currell, B., Eds. Inorganic and Metal-Containing Polymeric Materials; Plenum Press: New York, 1990. (c) Bergbreiter, D. E. CHEMTECH 1987, 17, 686.
30. Books and review on polymer-bound metal complex catalysts: (a) Gates, B. C. Catalytic Chemistry; Wiley: New York, 1992. (b) Sheats, J. E., Carraher, C. E., Jr., Pittman, C. E., Jr., Zeldin, M., Currell, B., Eds. Inorganic and Metal-Containing Polymeric Materials; Plenum Press: New York, 1990. (c) Bergbreiter, D. E. CHEMTECH 1987, 17, 686.